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Writer's pictureNick Gushue

The Brilliant Ambiguity of Black Sails

Updated: Nov 25



I’m not great at watching TV. Aside from the ritual of experiencing something my family enjoys at any given moment, usually a murder mystery procedural, I’m not one for committing for going through a series episode by episode. I’m not sure how I was recommended Black Sails, but the Starz pirate drama was somewhere in my mind when I decided this year to actually commit to a show. Initially, I understood it to be along the lines of other cable shows of the Golden Age of Television that encompassed the mid 2000s to mid 2010s: a violent, ensemble-driven drama about power, money, and sex. The Sopranos, Peaky Blinders, and Game of Thrones come to mind. Replace the mobs and gangs with pirates and merchant fences, New Jersey or Birmingham with Nassau, and strip clubs and pubs with a well-developed bordello and you have Black Sails. It never seemed to make it to that echelon however. And that’s a shame, because it’s honestly one of the best written of these dramas and I want to talk about it.

Almost every synopsis I can find about Black Sails brings up how it’s a prequel to Robert Louis Stevenson’s Treasure Island. And given how the overarching plot of the series is centred on claiming the Spanish gold of the galleon L’Urca de Lima and eventually the cache of gems that it is converted into, it’s easy to see how the show is a prequel. But there’s one way of seeing the show that hasn’t left my head since I first saw it on Twitter, where the show still has a strong and devoted fanbase.


This tweet references one of the most iconic moments of the series: The final confrontation between Silver and Flint in the show’s finale, “XXXVIII”, but in order to understand what Ithika is talking about, as well as what makes this finale so good, we need to understand what makes Black Sails so good as a series, whether or not it is a prequel.


I. 

A Story is True


What makes Black Sails so captivating to watch are characters and seeing how they play off of each other. The series does feature many of Stevenson’s pirates like Captain Flint, Long John Silver, and Billy Bones, but most of the supporting cast is made up of fictionalized versions of real figures of the Golden Age of Piracy, like “Calico” Jack Rackham, Anne Bonney, Charles Vane, Israel Hands, Edward Teach, and Woodes Rogers as well as many new characters like Eleanor Guthrie, the proprietor and primary fence of the stolen goods of Nassau; and Maxine, a sex worker who becomes exceptionally powerful in Nassau through sheer force of will. 

It’s not entirely relevant to the main point of this essay, but I would be remiss if I didn’t mention how, unlike shows like Game of Thrones or Peaky Blinders, sex work is portrayed with a considerable amount of nuance with most of the sex workers featured in the show being fully developed characters and sex work itself being integral to the political machinery of Nassau. I will also say the show is equally imperfect (especially in season one) at representing female sexuality outside of the male gaze with much of the queer representation that the show is known for initially being limited to erotic portrayals of sapphic

love, but this does improve and much of that eroticism is exchanged for compelling and complicated relationships that cross the gender barriers in myriad ways, but I digress. 

These characters, especially Flint, Silver, Eleanor, Vane, Jack, Anne, and Max, are each so well-developed with their own goals and motivations to such an incredible extent that even if you have a particular favourite character you want to succeed, you can’t help but root for the rest when they try to oppose your favourite and claim their own success, fortune, and power.

The two strongest characters are without a doubt Flint and Silver, who begin their journey as begruding allies when Silver makes it impossible for the treasure hunt to succeed without him, eventually becoming comrades and even friends that respect each other to the point that Billy Bones laments how impossible it is to truly know where Flint ends and Silver begins. 

Flint and Silver initially function as foils in the traditional sense due to their contrasting personalities and unlikely similarities. Silver is more juvenile and concerned with the current situation while Flint is more serious and focused on the grand plan, however both are equally opportunistic and cunning. In the first episode alone, Flint uses the loss of the Urca’s schedule to put down a mutiny by framing his challenger as a thief while Silver lies about being a cook to avoid being killed by Flint’s crew. Both are cunning, strong willed, and charismatic leaders who use story as their greatest weapon. However, as they grow closer, they are instead better understood as foils because of how the power of story affects the other. Story is the defining connective tissue between the two, as it is ultimately part of what divides them into who they are. 

Flint is more of a fictional character than Silver or anyone else on Black Sails, as he was once James McGraw, and the name of "Flint" came from a story his grandfather told him. He encountered a sailor named Flint who appeared and vanished as though conjured by the sea itself. He saw the name and the role of “Captain Flint” as necessary to his goal to reconcile Nassau with England, a plan he formulated with his former lover, the aristocrat Thomas Hamilton, before they were discovered and separated, cast across the sea. 

When Miranda Barlow, Thomas’s wife and Flint’s friend, is killed when they attempted to reconcile Nassau and Charlestown, Flint accepts the role of monster that “civilized” society believes him to be, regardless of what he has done. He begins a rampage across the English colonies that grows to a full rebellion in alliance with a hidden camp of freed African slaves. In this war, Silver, now a quartermaster and often selfless crewmate, is "crowned" as “Long” John Silver, a pirate king of Nassau by Billy Bones's propaganda and instigation campaign against Britain. Silver, who resents authority and anyone who would try and define who he is, is written as the very thing he resents the most: An authority. 

This war, while certainly justifiable and righteous, is fueled and propelled by Flint’s rage. This rage and darkness becomes clear to Silver when he comes to believe that the woman he loves, Madi, the commander of the free Africans, has died, and he sees the world, however briefly, as Flint does. When Madi and Silver are reunited, Silver understands that this war is the senseless violence of a man who has lost everything and would burn the world if he could. All of the conflict, scheming, loss, and rage leads to “XXXVIII” and the ultimate brilliance of Black Sails


II.

A Story is Untrue


The finale takes place on Skeleton Island, an uncharted island that is foreshadowed to be the final resting place of the treasure and the conflict between the pirates of Nassau and the colonial authority of Woodes Rogers. 

In this battle, Silver encounters a cook, cowering in the hold, who begs for his life as he is “just the cook.” The parallel is clear. Silver, a coward who has been turned into a king through story, is meeting a man who four seasons ago he was not too different from. The story of “Long” John Silver and Flint’s rage has changed him. Eventually, Rogers is defeated, the pirates are successful, and all that is left is to recover the cache of gems that comprises the wealth captured from L’Urca de Lima. It is here that Flint and Silver come to a head over Silver’s commitment to the cause. This debate is a reprise of two conversations between Flint and Silver set shortly before season 4. As Flint attempts to train Silver in swordfighting, he realizes that he does not truly know who Silver was before he met him. He observes, correctly, that Silver’s story of being an unremarkable child from Whitechapel is not truly real and in fact Silver has inserted himself into Flint’s story and relationships.

Flint is the only character that is given flashbacks of his life before the series, as though his story has been set into stone. Silver is even more separated from these characters as he is the only major character without a relationship established before the show. All others have someone else who can recall an anecdote or provide context as to where they came from, but all Silver has is his word alone. 

Later, Silver argues that he believes that there is no storyteller imposing meaning or coherence upon this world and he sees no need in accounting the events of his life into one story. For Silver, the only meaning he believes anyone could divine is that this is a world of unending horrors. This is repeated when, on the island, Silver declares Flint’s war to not be a war, but rather a nightmare, and he wants it to be over. Flint justifies everything, all of the pain, the death, the darkness, with, in my opinion, one of the greatest monologues in television.


Flint has made multiple speeches, addresses, and pleas to others to convince them of his way throughout the series, and this is perhaps the most open and honest he is in the entire series. He is not just trying to convince Silver, he is trying to convince himself. There is nothing left to guard or conceal. He needs Silver to agree. But Silver does not, because he fundamentally cannot allow himself to fall back into that darkness again. Silver became like Flint, not just by allowing the rage to fuel him, but by allowing himself to want to impart meaning into that loss. In this respect, “Long” John Silver is unmade by Silver when he lets go of the story of the pirate king of Nassau. In the same way, Silver unmakes Captain Flint by reuniting Flint with Thomas Hamilton, revealed to have been incarcerated in a plantation near Savannah, Georgia, for troublesome members of the English aristocracy. Before Silver is able to do this, Flint makes one last plea that is essentially the defining message of the show along with Rackham’s own “A Story is True, A Story is Untrue”.



While there are several instances of this being proven true in the series, it is ultimately the case given the series’s connection to Treasure Island. Regardless of who Silver, Flint, and Billy Bones were, they will always been known by what Stevenson wrote them to be. This tragic inevitability is what Ithika was referring to by comparing how Treasure Island is all that remains of them after the story is finished.


III.

All that Remains…


Part of what I find brilliant and tragic about the ending of Black Sails is how it ends with multiple divergences from Treasure Island that have tragic connotations when considering how one leads to the other. And in order to explain what I mean, I want to posit a unique interpretation of the show based on one of the last shots in the series: Was Treasure Island written in the world of Black Sails

One of the last shots in the series is of Mrs. Hudson, Rogers’s chambermaid, reading Charles Johnson’s 1724 book A General History of the Pyrates to her children. This is part of a montage showing the fates of multiple characters connected by Rackham’s monologue about stories and how they survive because people want to believe them. Johnson’s book is one of the most well-known sources of the Golden Age of Piracy and is notably criticized for mythologizing the pirates described and popularizing them in modern culture. The book was notably a major source of inspiration for Treasure Island. I want to be clear that I don’t see this as a fan theory or that viewing Treasure Island as being written in the world of Black Sails is what actually happened. This is more of a critical lens for examining Black Sails as events that become twisted into a mythology that then inspires the story of Treasure Island. The appearance of A General History of the Pyrates would suggest this, as the stories of Jack Rackham, Anne Bonny, Edward Teach, and Charles Vane are told within that book as well. This reading sees the tragedy as one in which the “real” Silver and Flint become transformed into the monsters of Treasure Island.

When the series has finished, Flint, or rather, James Mcgraw is reunited with Thomas, Silver has let go of the treasure, Billy Bones is marooned upon Skeleton Island, and Benjamin Gunn is not. James’ state is not clear. When explaining to Madi what happened to Flint, Silver describes the plantation near Savannah as a place where “men who enter these gates never leave them. To the rest of the world, they cease to be”, and alongside Madi’s disbelief that Flint would allow this, the implication is that Silver imprisoned James within it. Thus, James is reunited with his love but at the cost of the freedom he so fiercely fought for. This is how many people interpret the ending, but there’s a frustrating uncertainty in this interpretation. For one, although Flint would not accept it, Silver has made clear Flint has been unmade, in other words, ceased to be. For another, Flint is reunited with Thomas after the shackles on his wrists are unbound. All that is known is that Flint is brought here, money is exchanged to the plantation owners, and an unchained James is reunited with Thomas. All that matters to everyone else is that Flint is gone, and in Treasure Island, Silver claims he died in Savannah, Georgia.

Whether free or imprisoned, Flint’s ambiguous fate is much fairer than the others in the context of becoming the characters of Treasure Island. Benjamin Gunn is seen escorting James to the plantation after escaping Skeleton Island with the rest of Flint’s crew but ultimately becomes marooned on Skeleton Island three years prior to the events of Treasure Island with nothing concrete to suggest what events led him back to the island he believed cursed so long ago. In a similar vein, Billy Bones, the boatswain turned rival and traitor to the war, is left marooned on Skeleton Island. And considering the lack of the map that Billy carries to his grave in the series, Billy faces two endings. Either he escapes with knowledge of the treasure kept to himself and dies as a relatively "honourable" sailor in the Admiral Benbow Inn, or he dies forgotten, his name taken by Stevenson to use for the drunkard who leaves the treasure map for better men to find and claim. I don’t know which is worse. 

Lastly, and perhaps worst of all, is Silver’s fate. When he tells Madi what he has done, that he is the one responsible for ending the war with a compromise, unmaking Flint, and betraying her trust by doing both, she rejects him. Although, the final shot of Silver does have Madi standing by his side. Stevenson does describe Silver as having a wife, “a woman of colour” which suggests Madi remains with him and perhaps forgives him. Nevertheless, Silver, the man who abandoned the treasure so long ago, seeks it out again and returns to the account on the Hispaniola. Numerous times through the series, Silver laments at being in his position. He does not care for the sea or sailing and twice describes the events of the series as akin to a nightmare and full of horrors. Whether his legacy is twisted to fit a narrative that requires a monster or he finds himself compelled to return to the account for that treasure once more, Silver faces the fate that Flint warned him of. In the end, he would be distorted to fit the narrative and made into the monster of the story told to children.


IV.

Last Thoughts


When I first saw “XXXVIII”, I was honestly initially disappointed in Flint’s ending. When I saw how quickly it seemed for all of Flint's will to fade, I thought I had been betrayed. I expected a tragedy, for Flint and his rebellion to be sadly, but heroically, martyred and relegated to the footnotes of history by men like Rogers. And in that respect, I was consumed by Flint. Maybe it’s the part of me that believes mostly in Madi’s political philosophy, that sacrificing the righteous fight for a compromise was injustice. Maybe its that desire for freedom that truly motivated my interpretation of Treasure Island's nature as true fiction and not just inevitable, that there was some hope that Flint is free and with the man he loves, that Silver and Madi live unconsumed by the cache, and that there is something more to these criminals than the mythologies monsters of history and legend.

And the more I thought about it, the more I came to understand Silver’s position that what was done was the right thing to do, but I ultimately accept Rackham's position on story, that the story matters regardless of what has changed about it, that there is meaning to be found beyond the world being full of horrors. And that is what made me realize how brilliant the show was. That even if the ending was ambiguous, tragic, or hopeful, it still mattered. The story, true or untrue, still matters.


Special thanks to @Ithika for letting me use her post, you can find her here: https://twitter.com/Ithika


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